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Entourage authentication workarounds from MS and Apple

Monday, August 4, 2008

A reader who wishes to remain anonymous reports suggestions from Microsoft and Apple on how to deal with the problem of Entourage continually asking for a password. We've had a number of suggestions for this problem over the past few years. Bierman adds these suggestions:

The company I currently work for uses a hosted Exchange Server. We are having an inordinately high number of people who get the issue where Entourage will declare that your password was not accepted, but the same password works on OWA or outlook. So far the only fix that has worked is to dump the cache and re-sync. This fix is not permanent. We asked the hosting service to come up with a better answer. They opened an issue with Microsoft and worked out the following suggestions, but noted that none of them are true fixes, there is no true fix, and Microsoft has known about the issue for years with no fix in site. Here it is:

Q: Entourage will not accept your login information

A: There have been documented cases of Entourage 2004 and 2008 continually prompting for passwords and rejecting logins for users where the logins work in Outlook or OWA. Although we have worked with Microsoft on this issue, there is no known permanent fix for the problems at this time. Below are suggestions from both Microsoft and Apple on how to resolve the issues when they appear. We have listed them in the order of how successful we have found them to be in resolving the problems.

1) Change your Login information - Instead of using the information provided in <Control Panel Name>, please try one of the two authentication methods below:

Domain: [Leave Blank]

Account ID: Type in your Primary Email address

Password: Type your mailbox password


Domain: [Leave Blank]

Account ID*: Server\Mailbox Username

Password: Type your mailbox password

* Note - to create your account ID for this login workaround, you need to use your Exchange Server Domain and your mailbox username.

2) Delete any email with garbled or "odd" looking character sets

3) Remove any daily calendar reminders (turn off the reminders or remove or archive old appointments)

4) Empty your "deleted items" folder and "unk mail" folders

5) Remove stored passwords from the keychain:

OSX 10.4:

OSX 10.5:

6) Clear your font cache: Quit Entourage, open the following folder on your computer, and delete the two files listed below:


- - Tasman Browser.cache

  • Go to your Applications folder and launch Font Book
  • Select all fonts by holding down Command as you click on them * Go under the File menu -> Validate Fonts. This will bring up the Font Validation window.
  • If you see a checkbox next to the font then it means the font is OK. If you see a yellow warning sign, there may be a problem, and if you see a red "X" then the font is corrupt.
  • If corrupt, remove these by checking the boxes next to them and clicking "Remove Checked" at the bottom of the program window

7) Close Entourage. Launch a browser and log in to OWA (select "Private" to keep the session active longer). Once logged in to OWA, open Entourage and login. Once the OWA session times out, see if the password prompt returns.

If any of this works for you

For more on this topic, see our Entourage and Exchange Special Reports page. Comment below

TIP: Solution for Entourage password issue, caused by corrupt non-roman fonts

Thursday, August 28, 2008

An anonymous reader provided a solution to his previous report (above) about the problem of Entourage continually asking for a password. He previously offered a fix that worked only temporarily. His new solution is to identify email messages containing corrupt Asian-language fonts and remove them. Readers have previously identified messages with non-roman fonts as the problem, and fixed the problem by manually deleting the messages. Today, this reader offers a more automated solution that doesn't require deleting messages:

In the end the issue turned out to be malformed messages containing corrupt Asian-language fonts. The method for fixing them is to sync the account and watch the progress. When it stops syncing it will have gotten to a certain point, either an email in the inbox or a folder in the hierarchy. You can tell what folder it is working on by looking at the progress bar.

Then, using a PC running Outlook in online-only mode, take that folder (or specific email if your lucky enough to ID it) and remove it from the server, turning it into a PST file. Go back to the Mac and sync again. Assuming that was the only item that was bad it will finish; otherwise repeat as you hit each roadblock. When the sync is complete, go back to the PC and re-import all the items out of the PST file and into their proper place on the server.

Somehow during the server-to-PST-to-server migration, it cleans up the bad fonts/headers/etc and then (final step) you can sync it back to the Mac. So far this has worked on the first 5 machines it was tried on. For the record, I did not figure this out, but rather the credit goes to a co-worker.

If you tried this procedure

Note that other readers have offered other fixes that are not related to the non-roman fonts. In fact, elsewhere in today's news, a reader says that large attachments can cause the problem.

We've also previously reported that a Microsoft hotfix is supposed to address this problem.
Comment below

TIP: another solution to the Entourage/Exchange logon problem

Monday, September 22, 2008

Sigrid Neudecker found another fix for the Entourage/Exchange logon problem where it continually asks for a password. We've published a lot of different solutions from readers, the most recent of which are here. Neudecker sent us a new one:

I've been having this problem for almost 4 weeks now, since we moved from Germany to Paris. In my case Entourage seemed to get hung up while trying to synchronize my calendar. It would start downloading new messages but after a few minutes I get the "wrong password" prompt. When I quit Entourage and start it again it downloads new messages again as if nothing had happened but gets hung up on the calendar again after a few minutes.

I've tried deleting password from keychain, deleting deleted mails via webaccess, deleting the two cache files mentioned here. I deleted all calendar events with notifications, and exchanged the username with domain\username. Nothing worked.

Then, thanks to advice from a colleague I changed the settings for the account. I entered the address I usually use for accessing my account via browser (OWA) in the field "Exchange Server" and it now works!

In my case it also had something to do with an Exchange of the certificate, which our admin did, but I think it could have worked even without that.

If you've tried this approach to the problem
Comment below

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